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Remembering the Carl Crawford choice as free agency heats up

Brian Cashman’s infamous dinner is a reminder of how to treat this process.

MLB: New York Yankees-Workouts Kim Klement-USA TODAY Sports

It’s that time of the offseason, before any of the major free agents have signed, that the Yankees seem simultaneously rich and poor. The luxury tax limit has been reset—New York is going on a spending spree! But actually, the front office is shocked at the prices the Carlos Correas and Corey Seagers of the world are commanding and they might settle for a lower tier player.

It’s easy to get whiplash from from all of the leaks from the front office in November and December, the vacillation from superstar free agent targets to Andrelton Simmons. However, one incident from over a decade ago serves as an example to take what you hear with a grain of salt—and remember not to take everything at face value.

It was in the winter of 2010 that one of the best free agents on the market was outfielder Carl Crawford. He’d spent eight years tormenting the Yankees as a member of the Tampa Bay Rays. MLB Trade Rumors ranked him the second-best free agent on his class, behind only the coveted Cliff Lee. So when he signed a seven-year, $142 million contract, the main surprise was not so much the amount but that it was the Boston Red Sox who gave it to him.

Towards the end of the 2011 season, Yankees general manager Brian Cashman admitted to a bit of gamesmanship to drive the price of Crawford up on their rivals. At the time, he said, “I actually had dinner with the agent to pretend that we were actually involved and drive the price up,” Cashman said. “The outfield wasn’t an area of need, but everybody kept writing Crawford, Crawford, Crawford, Crawford. And I was like, ‘I feel like we’ve got Carl Crawford in Brett Gardner, except he costs more than $100 million less, with less experience.’”

Yet even someone as savvy as Cashman couldn’t have predicted just how much of an overpay Crawford would prove to be. The outfielder couldn’t muster even a full win above replacement during his time in Boston, managing just an 89 OPS+. His relationship with the team quickly turned so sour that he was traded to the Los Angeles Dodgers only two years into his contract. If Crawford had kept up his previous production with the Rays, Cashman wouldn’t have been able to direct his snark at the Red Sox, or at least it wouldn’t have landed in quite the same way. And while fans back in 2010 may have been distressed at the thought of spending tons of money on Crawford instead of Lee, it turned out, of course, that neither would ever be a Yankee, and both of their careers would end much sooner than anyone expected.

So, when Cashman in 2021 announces that the Yankees are “open for business” and especially interested in shortstops, then refuses to say if they’re even in on any of the major free agents like Correa and Seager, those soundbites are as much a business decision as anything else. Remember, everything the Yankee exec says right now comes with a purpose, an intention for someone to hear it. Maybe the Yankees have expressed trepidation about signing a start shortstop because they actually are reluctant, or, because they want other teams to hear that they’re apprehensive.

Yankee fans should save their their judgement for when actual signings are completed and dollar amounts are released. Otherwise, there might be a lot of getting worked up over nothing—or a decision that will pay off in unexpected ways with the benefit of hindsight, like Cashman’s craftiness over Carl Crawford.